Borane;tetrahydrofuran → HCID 58237949, compound

HRID 1192923Notes

Reaction equation

HRID 1192923 reaction equation
[CH2:1]([C@:4]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:9][CH2:8][N:7]([C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[CH3:11])[C:6](=[O:19])[CH2:5]1)[CH:2]=[CH2:3].B.C1C[O:31]CC1>C1COCC1>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([C@@H:10]([N:7]2[CH2:8][CH2:9][C@@:4]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([CH2:1][CH2:2][CH2:3][OH:31])[CH2:5][C:6]2=[O:19])[CH3:11])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 58109709HCID 58109709, compound

Product 1

HCID 58237949HCID 58237949, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-4-allyl-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)piperidin-2-one (70 mg, 0.169 mmol) in THF (5 mL) was added BH3/THF (0.6 mL, 1 M) at 0° C. under nitrogen atmosphere. The mixture was stirred for 2 h, and the reaction was quenched with water. Aqueous NaOH solution (1 M, 2 mL) and H2O2 (1 mL□30%) were added to the above mixture, and the resulting mixture was stirred for 1 h. The mixture was extracted with EtOAc, and the combined organic phase was concentrated to give the crude product, which was purified by preparative HPLC to give (S)-1-((S)-1-(4-bromophenyl)ethyl)-4-(4-fluorophenyl)-4-(3-hydroxypropyl)piperidin-2-one (30 mg, 41%). 1H NMR (CDCl3): δ 1.36 (m, 1H), 1.52 (m, 1H), 1.72 (m, 2H), 1.89 (m, 1H), 1.98 (m, 1H), 2.21 (m, 1H), 2.44 (m, 1H), 2.92 (m, 1H), 3.01 (m, 1H), 3.44 (m, 2H), 5.92 (m, 2H), 6.73 (m, 2H), 6.91 (m, 2H), 7.14 (m, 4H).

Workup

  1. customthe reaction was quenched with water
  2. additionAqueous NaOH solution (1 M, 2 mL) and H2O2 (1 mL□30%) were added to the above mixture
  3. stirringthe resulting mixture was stirred for 1 h
  4. extractionThe mixture was extracted with EtOAc
  5. concentrationthe combined organic phase was concentrated
  6. customto give the crude product, which
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-3437392f9ecc476a8c1b4b88dcc23b53
Source dataset
uspto-grants-2014_03
Patent number
US08680281B2

Reaction notes

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